Reactive diazo dyes, having a fibre reactive group containing a naphtylene middle component

Abstract

Reactive dyes of the formula <IMAGE> (1) in which A, U, R1, R2, Z and n are as defined in claim 1, are particularly suitable for dyeing or printing cellulosic fibre materials or naturally occurring or synthetic polyamide fibre materials with a high tinctorial yield and produce dyeings and prints with good fastness properties.

What is claimed is: 
     
       1. A reactive dye of the formula ##STR82## in which A is a radical of the formula ##STR83## in which R 5  and R 7  independently of one another are hydrogen, C 1  -C 4  alkyl or phenyl which is unsubstituted or substituted by C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 2  -C 4  alkanoylamino, halogen or sulfo, and R 6  is hydrogen, cyano, carbamoyl or sulfomethyl, or a radical of the formula ##STR84## in which R 8  and R 9  independently of one another are hydroxyl, amino or amino which is substituted by C 1  -C 12  alkyl, in which the C 1  -C 12  alkyl radical is unsubstituted or further substituted by hydroxyl, sulfo or sulfato and, with the exception of methyl, can be interrupted by oxygen, and R 10  is hydrogen, C 1  -C 4  alkyl, hydroxyl amino which is unsubstituted or substituted by cyano, or is phenyl which is unsubstituted or substituted by C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 2  -C 4  alkanoylamino, halogen or sulfo, or a radical of the formula ##STR85## in which R 11  is cyano, carbamoyl or sulfomethyl, R 12  is C 1  -C 4  alkyl and R 13  and R 14  independently of one another are hydrogen, a halopyimidine or halotriazine reactive radical which is further substituted or unsubstituted, or C 1  -C 12  alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato, in which the C 1  -C 12  alkyl radical, with the exception of methyl, can be interrupted by oxygen, or a radical of the formula ##STR86## in which R 15  is hydrogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 2  -C 4  alkanoylamino, halogen or sulfo and R 16  is phenyl which is unsubstituted or substituted by C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 2  -C 4  alkanoylamino, halogen or sulfo, or is a halopyrimidine or halotriazine reactive radical which is further substituted or unsubstituted, or a radical of the formula ##STR87## in which R 17  is hydrogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 2  -C 6  alkanoylamino, C 2  -C 8  alkoxy-carbonylamino, halogen or sulfo and R 18  and R 19  independently of one another are hydrogen, a halopyrimidine or halotriazine reactive radical which is further substituted or unsubstituted, or C 1  -C 8  alkyl which is unsubstituted or substituted by hydroxyl, sulfo, sulfato, phenyl or C 5  -C 7  cycloalkyl, in which the phenyl radical can be further substituted by C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 2  -C 4  alkanoylamino, halogen or sulfo and the C 5  -C 7  cycloalkyl radical can be further substituted by C 1  -C 4  alkyl, or a radical of the formula ##STR88## in which R 20  is hydrogen or C 1  -C 4  alkyl and R 21  is C 2  -C 6  alkanoyl, benzoyl which is unsubstituted or substituted by C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 2  -C 4  alkanoylamino, halogen or sulfo, or is a halopyrimidine or halotriazine reactive radical which is further substituted or unsubstituted, R 1  and R 2  independently of one another are hydrogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 2  -C 4  alkanoylamino, halogen or sulfo, Z is a group of the formula --CH═CH 2  or --CH 2  --CH 2  --Y and Y is a leaving group, n is the number 1, 2 or 3 and U is a reactive radical of the formula ##STR89## in which W is a group of the formula --SO 2  --NR 3  --, --CONR 3  -- or --NR 3  CO--, R 3  is hydrogen, C 1  -C 4  alkyl which is unsubstituted or substituted by hydroxyl, sulfo, sulfato, carboxyl or cyano, or a radical of the formula ##STR90## R is hydrogen, hydroxyl, sulfo, sulfato, carboxyl, cyano, halogen, C 1  -C 4  alkoxycarbonyl, C 1  -C 4  alkanoyloxy, carbamoyl or the group --SO 2  Z', Z' is as defined above for Z, E is the radical --O-- or --NR 4  --, R 4  is hydrogen or C 1  -C 4  alkyl and alk and alk' independently of one another are C 1  -C 6  alkylene. 
     
     
       2. A reactive dye according to claim 1, in which the radical --SO 2  Z is bonded to the naphthylene middle component in the 6- or 7-position. 
     
     
       3. A reactive dye according to claim 1, in which U is a radical of the formula (2), (2a), (2b) or (2d). 
     
     
       4. A reactive dye according to claim 1, in which R is hydrogen, W is a group of the formula --CONH-- or --NHCO-- and E is the radical --O-- or --NH--. 
     
     
       5. A reactive dye according to claim 1, in which Y is a group of the formula --Cl, --OSO 3  H, --SSO 3  H, --OCO--CH 3 , --OCO--C 6  H 5  or --OPO 3  H 2 . 
     
     
       6. A reactive dye according to claim 1, in which U is a radical of the formula (2), (2a), (2b) or (2d), W is a group of the formula --CONH-- or --NHCO--, R is hydrogen, E is the radical --O-- or --NH-- and Y is a group of the formula --Cl or --OSO 3  H. 
     
     
       7. A reactive dye according to claim 1, which contains at least one sulfo or sulfato group. 
     
     
       8. A reactive dye according to claim 5, in which Y is a group of the formula --Cl or --OSO 3  H. 
     
     
       9. A reactive dye according to claim 7, which contains at least one sulfo group. 
     
     
       10. A process for dyeing or printing fibre material containing hydroxyl groups or nitrogen, which comprises the step of applying to the fibre material a tinctorial amount of a reactive dye according to claim 1. 
     
     
       11. A process according to claim 10 wherein the fibre material is cellulosic fibre material or naturally occurring or synthetic polyamide fibre material.